


What's Under Your Pillow?

by Zaggiestan



Category: The Try Guys (Web Series)
Genre: Dildos, Early dating, F/M, Making Out, Mutual Masturbation, The Try Guys, Zaggie, ear nibbling, female orgasm
Language: English
Status: In-Progress
Published: 2021-01-18
Updated: 2021-01-18
Packaged: 2021-03-16 14:59:55
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,354
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28833066
Author URL: https://archiveofourown.org/users/Zaggiestan/pseuds/Zaggiestan
Summary: Maggie makes a kinky discovery, both inside Zach's pillowcase and inside the hidden places in her own mind.
Relationships: Maggie Bustamante/Zach Kornfeld
Kudos: 3





	What's Under Your Pillow?

**Author's Note:**

> ~Obviously this is just for fun based on the story that they've both told on their podcasts. I hope they don't find this but if they do, no offence is intended~

“Zachary, what’s that smell?”

Zach smelled it too. It was familiar to him. Like a kind of plastic meets rubber odor. He couldn’t quite place it. It seemed to only be present when the a/c was running. 

“Uh… I don’t know, Maggie. I smell it too. Maybe something is up in the vents. I’ll call the landlord to change the filters on Monday. I’m sorry,” he nervously pouted. 

“It’s not your fault, bubbie. It’s not that bad.” Maggie smiled sweetly, her dimples melting Zach’s heart. 

They had only been dating a short time but Zach already knew he was falling madly in love with Maggie. It was love at first sight for Zach when he met her in the gender neutral line for the bathroom at The Abbey. He’d never felt so strongly for any girl and he didn’t want to fuck it up. He knew Maggie was special. On their first date, he agreed to go to an ice cream place after they finished their Ramen even though he was allergic to dairy just to spend more time with her. Turns out she was lactose intolerant as well and just suggested ice cream as a way to keep spending time with him, a first date story they would laugh about for years to come. 

This was the first time Maggie was staying over at Zach’s apartment. He shared it with two other guys and it was basically a frat house, which was putting it nicely. It reeked of stale weed, beer, and whatever that rubbery plastic smell was and wasn’t very clean or organized; in other words it was the epitome of a “bachelor pad” - the ideal living situation for a guy in his mid 20s, which someone dating him will tolerate if he is worth it. Zach was definitely worth it; Maggie had never been treated with such respect by a potential boyfriend. The phrase “I’m going to treat you like a Queen” is thrown around by a lot of guys but this was the first time Maggie truly experienced it. Zach was so cute and lovable and didn’t try to be macho or manly. Maggie had never dated a guy who rejected toxic masculinity so thoroughly. Whatever he had experienced with “The Try Guys” at Buzzfeed, something Maggie was still wrapping her head around, must have been working. After all, Maggie wasn’t the kind of woman to make out with a guy she just met but couldn’t help herself with Zach when they met at that Gay bar. Maggie had no idea he was “internet famous” and was shocked when one of her girlfriends told her just how popular his videos were; she had recently watched them all, just curious, and she found them hilarious and refreshing but it certainly wasn’t the main reason she was attracted to him. His cute smile and big blue eyes constantly filled with wonder, glee, and excitement were too irresistible. 

After a casual dinner at a sushi place nearby, Zach and Maggie returned to his apartment and watched ‘Paddington’, which Zach so adorably insisted Maggie watch. He was so into the movie as they cuddled together that it made the already great movie that much greater. Honestly watching Zach’s reactions, laughing and excited as if he was watching it for the first time (though he had memorized his favorite lines so he’d obviously watched it several times) brought such joy to Maggie and made her laugh harder than she remembered laughing before. Was she falling for him? She’d certainly never met a guy like him before. 

After the movie, they each took a turn freshening up in the bathroom, brushing and flossing their teeth, before cuddling together in Zach’s twin bed, Maggie in a nightshirt and panties and Zach in an old pair of boxers he wore to bed whenever he had company (which wasn’t often). The air conditioner kicked on and that strange plastic-y smell came back. After he turned off the lamp, and placed his glasses on the nightstand, Zach gently kissed Maggie who loved the feel of his soft, warm lips against hers. Maggie cuddled into Zach’s arms, hugging him close to her, and laid her head on his pillow. 

A few minutes later, Maggie was struggling to get comfortable. Zach’s pillow was lumpy. 

“Lean up for a second so I can fluff the pillow, cutie,” Maggie said softly; Zach obliged. As Maggie fluffed the pillow, she felt something hard beneath it in the pillowcase. 

“Zachary?” 

“Huh?” he replied sleepily. 

“What’s this hard thing under your pillow?”

“What hard thing?” he replied, his voice already layered with grogginess. 

“There’s a hard thing in your pillowcase underneath your pillow,” Maggie said, her voice holding a note of confused curiosity. 

Zach felt himself waking back up fast, wracking his brain to understand what she was talking about. “Umm… I don’t know…” suddenly it clicked into place, “OH SHIT!” Zach yanked the pillow away from her, reached inside and pulled out a giant black rubber dildo which Maggie could make out the silhouette of against the dim light coming in the window from the street light outside. He threw it across the room, and looked away from her face, embarrassed. “FUCK! Ugh!”

They sat for several moments, which seemed much longer, in awkward, uncomfortable silence. Maggie was more confused than anything, although at least the mystery of the source of that latex-like smell was cleared up. Maggie didn’t know if Zach used that toy with other girls he brought home, or... something else? The former thoughts made her feel uncomfortable, but the unspoken latter… what was the emotion she was feeling? It was time to break the silence. 

“Umm… Zachary?” Maggie said timidly. 

“Uh… yeah?” Zach replied, his voice trembling with anxiety. 

“Why was a giant dildo in your pillow?” Maggie asked. 

“Uh… don’t worry about it; it was nothing. Goodnight.” Zach laid down and turned away from her. 

Maggie reached over him and turned the lamp back on. Zach looked over his shoulder and met her eyes, tears welling up in his own panic stricken blues. Maggie’s heart melted at the sight of him looking so afraid and disappointed. 

The words rushed out of Maggie’s mouth: “We didn’t have the talk about exclusivity so if you use it with someone else, we can talk about it, as long as you’re being safe. I just really like you that’s all and I would like you to just be honest with me if there’s someone else in the picture.”

Zach’s eyes widened in surprise, internally kicking himself; of course she would think that! “There’s no one else! I really like you too! I promise I would tell you if I was! I can’t believe I fucked this up!” 

Maggie frowned in concern and sadness, “No, bubbie, you haven’t fucked anything up. It’s okay! … Well…” she hesitated before continuing, “if you use it on yourself, that’s okay too… a lot of people are into different things and I just need to know if that is... one of your kinks… so I can be a part of it?”

Zach smiled and started giggling, which turned into a bigger laugh. Maggie started laughing too, still confused but glad to release the tension of the moment. They laughed for a couple minutes before they were able to contain themselves. 

“What?” Maggie managed to say between laughs. 

“Maggie, you’re so great!” Zach giggled out. “I don’t use it sexually! It’s just a joke thing.” 

Maggie still was confused. “What do you mean?” she asked, “Why was it in your pillow? I don’t understand.” 

Zach sat up and gave a sweet smile. “Okay, okay, this is going to sound really stupid and immature, but here goes: A while back, I was the production assistant on a music video shoot for the comedy band Lonely Island, you know Andy Samberg’s group.”

“Okay…” Maggie said, still confused about where this was going. 

“And they had a ton of dildos for their music video and I took a handful home in case they were ever useful in a funny Buzzfeed video,” Zach explained, nervously. 

“Okay…” Maggie repeated, frowning. “But… I still don’t understand how it got under your pillow?”

Zach gave an embarrassed grin. “Well, it’s really stupid and immature,” he giggled, “buy my roommates and I use them to prank each other. Like sometimes we suction them inside the bathroom cabinets or put them in the fridge or hide them in each other’s suitcases when we travel home to visit family. I know it’s so stupid. I’m sorry you had to find it like that!”

Maggie smiled widely at him and took his hand, lacing her fingers between his. “It’s okay, cutie! No need to be embarrassed. Your sense of humor is one of the reasons I like you. It’s not a big deal!” She leaned in and kissed Zach tenderly, her hand caressing his cheekbone. 

Their lips parted and Zach’s soft, gentle tongue started exploring Maggie’s mouth. Maggie’s hand started softly playing with the thick hair on Zach’s chest and his hand slipped under the nightshirt she was wearing and he cupped her small breast in his hand and started delicately pinching her nipple. Maggie moaned softly into Zach’s mouth. 

Zach pulled away suddenly, as a thought occurred to him. 

“What’s wrong?” Maggie asked. 

“Nothing’s wrong!” Zach replied enthusiastically, smiling in wonder. “You were prepared to be okay with it if I used the dildo on myself!” 

Maggie blushed, embarrassed, her chocolatey brown eyes widening slightly. “I… uh…” 

Zach smiled wider and started giggling, “You were actually going to help me if I was some kinky bastard who uses dildos! Wow! You’re incredible!”

Maggie smiled back, still blushing. She was too embarrassed and confused to continue this conversation right now so she once again locked lips with the cute boy whose arms were wrapped around her. They began fondling each other’s chests again. Maggie climbed on top of Zach and trailed her hand down his hairy chest and thin stomach and began groping the outside of his loose boxers. Zach let out a squeal as her hand brushed the fabric against his quickly stiffening boner. His hands were now both under her shirt and caressing her perky breasts and hard nipples. 

Maggie slid her hand into the waistband of Zach’s boxers and grabbed his thick hard erection, making him give out a lustful moan. His tongue in her mouth became more ferocious as he began thrusting against her hand. Meanwhile, wanting to give her as much pleasure as she was giving him, he broke the kiss so he could wet his fingers in his mouth. He made a show of sucking on his fingers before trailing one of his hands down her petite frame and into her warm panties then sliding his fingers gently into her wet vagina. It was her turn to moan as he slid his middle and ring fingers inside her and softly started circling the head of her hard clit with his thumb. 

While Maggie moaned still stroking Zach, he kissed her neck, humming into her flesh. Maggie could feel his light scruff against the skin of her collarbone which only heightened the pleasure all his fingers were giving her: one hand softly pinching her nipples and cupping her breasts; the other in her panties, fingering her hot wet pussy and stroking her clit. She knew she was close and started grinding and gyrating, fucking his hand. Zach let his fingers remain still so Maggie could use them to fuck herself and started rubbing her clit with his thumb in quicker circular motions. Meanwhile, he could feel himself getting closer to cumming as Maggie's hand continued to pump his cock. 

Their mouths and tongues locked once more as they moaned loudly together, both racing each other toward the blissful release of orgasm. Maggie got there first. She released his cock as she panted, “Oh, yesss, bubbie! Right there, Zach! Mmmmm so good. Yessss!” she shivered from head to toe as tingling waves of pleasure washed over her for several moments. She smiled, satisfied, and found Zach’s soft, sweet lips again, gently caressing his tongue with hers. She looked lovingly into his lusty deep blue eyes and gently rubbed his cute little nose with her own. 

Maggie reached back inside Zach’s boxers and grabbed his raging hard cock once more, continuing to pump. Zach moaned loudly, and started thrusting his cock inside her grip, seconds away from cumming. 

Maggie leaned in closer to him, trailing soft kisses along his jawline until she found his ear. She gently nibbled on his earlobe, eliciting high pitched squeals from the sexy man beneath her, while she sped up stroking his cock and he fucked her hand with urgency. Zach could feel and hear Maggie’s hot breath against his ear. She whispered softly, “Ohhhhh my goddddd… you’re the clitorisssss”

Zach’s eyes flew open in wide shock at the reference to his infamous line in that stupid costume video, laughing, as the head of his cock swelled and shot ropes of cum into his boxers, Maggie’s hand still wrapped tightly around him. “OH FUCK! OH FUCK YES!” Zach yelled, as he came harder than he had ever come before. 

Maggie removed her hand from Zach’s softening dick as they kissed and cuddled up against each other, Maggie still on top. Zach broke the kiss, a blissful afterglow grin still settled on his mouth. “Mmmmm, if I knew it would excite you that much, I would have hid the dildo in my bed myself!” Maggie blushed, alarmed eyes wide, and looked Zach in the eyes, searching to see if he knew the naughty thought that had been hiding at the back of her mind ever since she found the dildo; the thought she wasn’t ready to voice. 

When Zach fell into a fit of giggles and laughter at his joke, Maggie let out a sigh of relief and cuddled into his arms, laughing with him. She kissed him once more and they settled into a comfortable silence that was soon followed by a satisfied sleep.

**Author's Note:**

> I hope this was as fun to read as it was to write. I have some ideas for where I want the story to go in a couple more chapters but I welcome feedback. Please add comments and tell me what you think!


End file.
